If you're looking for a film with a deep message you can learn from or read into then limiting yourself to 'philosophical' film won't get you anywhere. There are thousands of movies out there which will change the way you think in a powerful way without being a straight up lesson in philosophy.
Abel Ferrara’s The Addiction. Philosophy student come vampire living in New York, struggling to come to terms with life and being a blood sucker. Inevitably pretentious due to the subject matter but you do get a cameo from Christopher Walken and Lili Taylor is brilliant as always. It reminded me of her role in I Shot Andy Warhol. Very deep dialogue and numerous philosophers quoted if that’s your bag. Some of it was slightly over my head but that the whole fun of philosophy!
Another fine example of educated film with a message has to be Six Degrees of Separation with Will Smith. Don’t be put off by Big Willy; he is absolutely fantastic as the troubled young street punk with psychological problems and a head for philosophy. It really changed the way I think about art and literature, and also made me go back to study The Catcher in the Rye again.
I don’t think that true philosophical theory translates well on to film; this is why I haven’t bothered to seek out a copy of Sophie’s World on DVD. The extremely abstract concepts of some philosophy can be hard to mould around a plot and characters. Stick to the books, impossible to beat.
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